Electrostatic charging of insulators is well known to pose potential threats to electronic systems under terrestrial systems. We were asked to evaluate potential hazards associated with replacement of an electronics board in the vacuum of space during the upcoming Hubble Service Repair mission in September 2008. A device called a "tribot" was built to simulate triboelectric charging of several insulators that are capable of contact charging against astronaut's gloves and suit materials. Materials were evaluated as the extent of not only the magnitude of electric fields generated by the frictional action, but also any resulting discharge which would be a source of EMI. Experimental results are quite surprising and unexpected when compared with tests performed under ambient conditions under dry and humid air.